


You're Unbelievable

by igotout



Category: Supernatural
Genre: Anal Fingering, Ass Play, BDSM, Breathplay, Cock & Ball Torture, Cock Warming, Coercion, Come Eating, Daddy Kink, Dom Castiel (Supernatural), Dom/sub, Dubious Consent, Edgeplay, Forced Prostitution, Frottage, Humiliation, Intercrural Sex, M/M, Mild Painplay, Organized Crime, Panties, Semi-Public Sex, Sexual Content, Spanking, Sub Dean, Team Dean Winchester's Red Ass, but very mild cbt, maybe more in the future idk
Language: English
Status: In-Progress
Published: 2020-04-08
Updated: 2020-11-16
Packaged: 2021-03-02 02:26:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 20,361
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23527609
Author URL: https://archiveofourown.org/users/igotout/pseuds/igotout
Summary: Dean is coerced into a situation that requires a career change. His new position is at the feet of a powerful and mysterious man.This is mostly just porn strung together with minimal plot, you're welcome!
Relationships: Castiel/Dean Winchester
Comments: 86
Kudos: 274





	1. Other Options

**Author's Note:**

> Please read the tags! They'll be updated as I post. 
> 
> Title from Lana Del Rey's 'Million Dollar Man'. 
> 
> _"If you're going crazy, just grab me and take me"._

**Notes for the Chapter:**

> Hello, welcome to the long awaited Crime Boss AU! 
> 
> It's important to note that this isn't a roadmap for healthy and safe BDSM, it's a fantasy where things are a bit dangerous and risky. Please do not be this cavalier about BDSM in real life! Technically Dean is coerced into this position so the entire fic is dub-con at best so if that's not your cup of tea, then please be careful reading this. :)
> 
> Title from Lana Del Rey's 'Million Dollar Man'.
> 
> _"If you're going crazy, just grab me and take me"._

It was a Tuesday night and Dean was in the backseat of a black SUV—a Rolls Royce, with tinted windows and a mini-fridge. The doors were locked and he couldn’t see a button to unlock them again, not that he’d try to if he found one. There was a stocky, bald-headed man in the driver's seat, with a similar looking guy riding shotgun. There was another goon in the back next to him, sitting quietly and staring straight ahead. What a boring job, Dean thought.

They’d appeared at the bar, just after ten. Dean had been serving drinks; cold beer to cold men coming in from the cold snow to watch whatever game was on. He was pissed off enough as it was, what with John leaving the day before, out of the blue. Back into the blue. Dean had no idea where he’d gone. And then these idiots added to it.

Dean watched the headlights of the cars on the other side of the median, streaming past him, coming from Chicago back to Milwaukee. He sighed. A trip into the city this late at night was going to be a bitch to deal with tomorrow. Dean figured he wouldn’t get back until close to four at this rate. Although it wasn’t like he had much of a choice.

Dean had just been standing quietly, wiping glasses down when one of the thugs, wearing a crisp black suit with a tie that looked tight enough to choke him, had come up to the bar, beckoning Dean over.

“You Dean Winchester?” the guy said.

“Who’s askin’?” Dean answered, polishing a glass as he squared his shoulders, ready to stare the guy down if need be.

“My boss.”

“Yeah? Who’s your boss?” Dean asked, switching the shined glass out for another.

“Genesis Enterprises,” the thug said, as if that was supposed to mean anything to Dean.

“Don’t know ‘em,” Dean said, holding steady eye contact.

“Yeah, well we know you. You owe us money,” the man replied, staring right back.

“I don’t owe anybody anything,” Dean said, his tone icy as his patience wore thin. He put the glass down and crossed his arms.

“John Winchester owes us money,” the thug said, “But we learned that he’s left town. That means you owe us money.”

Dean felt like the bottom of his stomach had dropped out. That explained his father’s hasty exit then.

“Borrowed cash from a loan shark, huh?” Dean said, feeling bitter, “Sounds like his problem.”

The thug considered him for a moment, before resting his forearms on the bar, leaning in to speak quietly as though they were co-conspirators, or old friends. Dean noticed how thick his neck was, the same width as his head. It was weird.

“You see Dean,” the guy said, “It’s very much your problem, because my boss wants what he’s owed. And if you refuse to take ownership, to be a man and deal with your responsibilities, we can make this your brother’s problem.”

Dean’s jaw clenched before he could stop it.

“We looked him up, little Sam. Scholarship to University of Chicago, that’s pretty impressive. Would be a shame if he had to drop out due to financial hardship. Or smashed knee-caps,” the thug stood straight again, “I’m kidding, we don’t do that anymore. Much.”

He smiled at Dean. It wasn’t friendly.

“Okay,” Dean said, running his hand over his jaw, “Alright. I finish around midnight, can we talk then?”

“You finish now. Let’s go.”

Dean had had no choice but to collect his wallet and go with the men, the main thug and the two other, thinner-necked thugs. They’d walked him out to the Rolls in the parking lot, standing uncomfortably close as they did so, before all but pushing him into the backseat. They took his phone.

Dean leaned his head against the window, watching as the lights of Chicago approached. He felt sick, a dull throb behind his eye and his guts like lead as he thought about his father.

Dean had only just seen him on Monday morning, in the living room of their small rental place.

They hadn’t been there long, barely six months, but already Dean had watched his father hurriedly stuff his things in a duffel bag, oblivious to mistakes as he packed all his shirts but only one sock, grabbing things at random from the basket of clean laundry on the couch. Laundry that Dean had done for him.

 _Milwaukee isn’t the place for me,_ were the words he’d used as he tried to explain, mumbling and not looking Dean in the eye as he moved hastily around the room. _You’ll be fine here, Sam’s only an hour away._

Dean hadn’t said anything. He’d felt disappointed, but only in himself for hoping that his father would stay this time.

 _You’re the one who made us move here,_ he’d wanted to say, but didn’t. In reality, Dean was nearly twenty-six years old and should be able to make decisions for himself. If he couldn’t say ‘no’ when his father suggested they up and move cities to be close to Sam, that was on him and he knew it.

Dean believed the line John fed him, time and time again, telling himself that a new beginning with a fresh perspective might be enough to calm John’s nerves, to help him settle and want to be a father to his adult sons. He knew John was a drifter and a dead-beat but still, his stomach soured every time John proved him right.

“So where are you going?” Dean had finally asked, his eyes fixed on a spot on the floor.

“Dunno,” John replied, barely more than a grunt.

Dean had rolled his eyes, but only because he’d known John wasn’t looking.

“You gonna stop by and see Sam on your way out?” Dean asked, at least trying to figure out if his father was heading east through Chicago or not.

John merely shrugged. He tugged on the duffel bag’s zipper and, to Dean, the sound felt deafening in the quiet of their shitty apartment.

“Well,” John had said, “See you round.”

Dean said nothing as his father walked out the door without so much as a glance in his direction.

“You’re an asshole,” Dean had said to the silence of the empty living room. He’d immediately felt childish, unable to say it to John’s face, and knowing John wouldn’t care if he did. It was maddening.

He was pulled from his thoughts as the Rolls took a sharp corner, pulling up at a nondescript parking garage.

“We’re back,” the thug in the driver’s seat said into a cell phone, “We’ll be up in five.”

The garage door in front of them started lifting up, and Dean took a deep breath as they entered the bowels of the building. Into the belly of the beast, he thought to himself. Whatever that meant. Maybe they were going to kill him, although that wouldn’t get anybody their money back. Hopefully whoever this mafia-wannabe asshole was, he’d let Dean work out a payment plan. He remembered what his uncle Bobby had told him—hope for the best; prepare for the worst.

Dean was escorted through the parking garage, past rows and rows of other shiny black cars of all different makes and models. This level of the garage alone probably had millions of dollars worth of assets in it. Whoever John had screwed over, they were incredibly rich. That made them dangerous. Dean would have to do what he could to keep them away from Sam.

The goons led him over to the elevator, crowding around him once they got inside. Thick-neck pushed the button for the twenty-fourth floor, and Dean swallowed, trying to think of the last time he was that high up off the ground.

He was then escorted from the elevator and down a long hallway. It felt like a maze, in the setting of an expensive modern office building. Finally, he was shown into a small office.

It was really, really small. And sparse. There was nothing but an empty desk with a chair on either side, and one large window that stretched from floor to ceiling. Thick-neck pushed him into the chair in front of the desk, as though this was some sort of waiting room. Dean looked over his shoulder, watching him step back outside and take up a place at the door. Guarding him.

There would be no chance of escape, then. Dean sighed.

There was a clock on the wall, so he knew it had been seventeen minutes, just sitting there, with nothing to look at but a terrifyingly high view of the city. There was one lamp in the corner, so the light in the room was low, casting long shadows across the deep gray carpet. Better than an interrogation lamp right in his face, Dean supposed.

Suddenly, he heard the door swing shut behind him. Before he could turn, a woman entered his field of vision, stepping gracefully behind the desk, taking the seat opposite him. She had a thin manila folder with her, but she didn’t open it.

“Dean,” she said, smiling politely as though he hadn’t been hauled here in the middle of the night against his will, “My name is Hannah, I’m here to discuss your small debt problem.”

“My father’s debt problem,” Dean interjected.

“Well. He’s not here, is he? That makes it your debt,” Hannah said, still smiling.

“I don’t think that’s how debt works,” Dean replied, frowning a little at her explanation.

“It’s our money, and we say that’s how it works,” she said, her posture as casual as if they were friends meeting over coffee, “Now, let’s discuss your options.”

She flipped open the manila folder, taking a brief look at the graph on the paper.

“From your file here, it says you owe one hundred and fifty thousand dollars,” Hannah said, closing the folder again, “Are you able to pay that back in a lump sum?”

“What do you think?” Dean snapped. Yesterday he’d thought about opening a savings account. Today he apparently owed some loan shark one-fifty large because his piece-of-shit father was being a piece of shit again. Sometimes life liked to kick you while you were down.

“We do have openings, if you’d like to work off your debt,” Hannah said, ignoring his remark, “If you were to start with us immediately, you’d be put into Debt Collection.”

“Right, so that would be going around with those assholes out in the hallway, intimidating people?” Dean asked.

“Essentially,” Hannah replied, “Are you at all squeamish?”

Dean raised his brows, not sure exactly what she was suggesting.

“There is an element of... Force involved with this position,” she explained, “And some disposal.”

“You want me to be a thug?” he asked, “You want me to shake down desperate people for money they don’t have?”

Hannah just spread her hands in front of her, as if to say that was exactly what they wanted from him. She was still smiling.

“Fuck off,” Dean said, “I’m not doin’ that. You can smash my kneecaps in if you want, but I’m not gonna go around hurting people just because you decided I owe you money.”

“You do owe us money,” Hannah replied.

Dean rolled his eyes.

“Can’t I just send you a portion of my paycheck? Isn’t that how normal people pay back loans?”

“Sure,” Hannah said, “But if you don’t actually work for the company, then the loan will accrue interest. You’d owe more and more every month until the debt was doubled and then we’d have to smash your skull in.”

Dean just stared at her.

“I’m kidding,” she said, “Mostly.”

“I can’t—I’m not going to hurt anyone. Please,” he said, hoping he didn’t sound like he was begging, “There’s got to be another option. Like a janitor, or a receptionist or something. You got a bar? I’m a great bartender.”

Hannah leaned back in her chair, considering him for a moment.

“I may have something for you,” she said, “Sit still for a moment.”

Dean watched as she pulled out her phone and took a photo of him. He blinked his eyes, trying to get rid of the shadow in his vision that the flash had left behind. Hannah was typing something, her thumbs moving at lightning speed, her entire focus on the screen as it lit up her face.

“Right,” she said, standing up when her phone chimed after barely a minute, “Come with me.”

“Where are we going?” Dean asked, hesitating before following her out the door.

“To see about your other option,” she replied.

They walked back down the labyrinth-cum-hallway, the thugs following along behind, before stepping into the elevator once again. This time, Hannah pushed the button for the forty-ninth floor. Of course they’d have to go up even higher.

It didn’t take them long to get there, and Dean was led down a much shorter hallway, this one furnished much more like an expensive apartment building than an expensive office. They came to a stop outside a pair of exquisitely carved double doors, made of a heavy dark wood.

Hannah pushed the buzzer on the intercom, just to the right of the doors, and waited for a response. There was an audible sound as the lock tumbled, and Hannah pushed one of the doors open.

“Through here,” she said, gesturing for Dean to keep following her.

The apartment they entered must have been the most expensive place Dean had ever been. Shiny floors with marble tile, expensive looking rugs, art on every wall. The chandelier above him glittered like it very well might be made of diamonds. Dean was so busy watching light sparkle off of it, he didn’t notice the other man in the room until he spoke.

“Thank you, Hannah,” came a deep voice, and straight away Dean turned to find it’s owner.

The man was handsome, that much was obvious. Dean heard the door lock again as Hannah closed it behind her on her way out, but he kept his eyes on the man before him. This must be his Other Option.

They must be about the same height, Dean thought, but his Other Option seemed so imposing. He had dark hair and bright eyes, blue like the sky as dusk settles. He wore a suit, a nice one, and while it hid the finer points of his figure, Dean could tell that this guy was stacked.

“Hello, Dean,” the man said to him.

“Hello,” Dean managed to say back.

“Come and sit down,” his Other Option said, gesturing to the huge sectional sofa in the split level living room behind him.

Dean was cautious, his eyes never leaving the man as he stepped down into the living room, taking a seat at the end of the sofa. It was white leather. Who in the hell had a white leather sofa? Insane people, Dean figured.

The man sat down opposite him, on an expensive looking square ottoman that was large enough to seat four people.

They considered each other for a moment.

“Hannah says you’re having some debt troubles,” his Other Option said to him.

“My father has some debt troubles, your girl Hannah says it’s my problem now,” Dean replied.

“Yes, that’s generally how it works here,” the man said. His gaze was piercing and Dean had to focus on breathing to make sure he kept doing it right.

“Sounds a bit unfair, don’t you think?” Dean managed to say.

“Life’s unfair,” the man replied, watching him with loosely clasped hands resting between his knees.

Dean rolled his eyes, just a little, feeling exasperated with everyone telling him that his father’s fuck up was his to deal with. That’s what people said when they wanted to screw you over.

“Look,” Dean said, “Hannah said that if I don’t want to bust kneecaps, you’re the guy I should talk to. Is that right?”

“Yes,” the man replied, looking at Dean so intently that a shiver went down his spine, “I do have an... opening, of sorts. A position within my personal staff that I would very much like to fill.”

Dean thought that over for a moment, unsure as to what the man was implying.

“Like a butler?” he asked, finally.

“Not quite,” the man replied, eyes seeming to twinkle at him.

“I mean, what then? A bodyguard? A personal assistant?” Dean was sure he’d be terrible at any of those, but it was better than the alternative. Not being here would be an even better option, but all Dean could think about was Sam sitting where he was now. It couldn’t happen.

“Do you know what a courtesan is?” the man asked him.

“That’s—” Dean frowned, thinking for a moment, “That’s a fancy word for sex work. You want me to find you a courtesan?”

His Other Option smiled at him. It wasn’t menacing, but it wasn’t exactly friendly either. He smiled like he was laughing at Dean.

“I want you to be my courtesan,” he said, calm as anything, as though those words didn’t bring Dean’s brain to a crashing halt.

“Pardon?” Dean managed, finally, after a good few seconds spent staring at the man with his mouth agape.

“I would like you to join my staff as my courtesan, in exchange for paying off your debt,” the man explained.

“What if I wasn’t into men?” Dean asked.

“Are you into men?” the man asked him back.

“Sometimes,” Dean replied, blushing a little. It wasn’t a well known fact, but he’d come to accept that that’s how he was.

“Then I don’t see a problem,” his Other Option said, still considering Dean with a twinkle in his eye.

“So..,” Dean swallowed, “So, we’d be fucking?”

The man’s smile widened.

“Among other things,” he said, “More specifically, I’m looking for someone who can do as they’re told.”

Dean looked away, his gaze drifting to the city beyond the huge windows. He needed a moment to think. It wasn’t like this man was ugly. Unless he was into some weird kinky shit, Dean could do a lot worse than fucking this guy on the daily.

“So... I come here and just bend over when and where you tell me to?” he asked, shifting in his seat.

“Essentially,” he heard the man say. God, none of these people could give him a straight answer.

“Okay, but there are rules right? Like for kinky bondage shit, there’s rules to stay safe,” Dean felt panic rising in his chest, but tried to breath through it, trying to maintain at least some sense of composure.

“There are definitely rules. Ones that I make, that you will adhere to,” the man said, and shit, his voice was so nice.

Dean needed to focus.

“Do I get a safeword?” he asked finally, looking back at the man across from him.

“Do you think you’ll need a safeword?” his Other Option asked in response, staring right at Dean like he could see into his very soul.

Dean tried to focus, shifting his brain from the man’s strong jaw line to the words he’d said. Dean frowned.

“You just told me I can be either your personal whore or beat people up, all because of some bullshit debt that you’ve decided is my problem. With you, I want a safe word.”

“Fair enough,” the man replied, still smiling, “If you feel unsafe, you may say ‘safe word’. But, please do bear in mind, if you use the safeword constantly to get out of every single thing I ask of you, I’ll have to send you back to Hannah for reassignment.”

“Fine,” Dean said.

“Now... Can you follow orders, Dean?” the man asked, his voice casual but low enough to suggest otherwise.

“Is that what you want from me?” Dean replied, feeling unmoored and increasingly lost.

The man stood, seeming to tower over him as he stepped into Dean’s personal space.

“I want you to be a good boy, Dean,” he said softly,his fingers brushing through Dean’s hair so lightly that it was almost imperceptible, “Will you do that for me?”

Dean swallowed thickly, trying to gather himself.

“Yes,” he said, heat rising within him as he fell more under the man's spell.

“Yes, what?” the man said.

“I—,” Dean paused, “I don’t know your name.”

“You don’t need to,” the man said, staring down at him, like he could pin Dean in place with his eyes, “Call me Sir.”

Dean recoiled at that, pulling away from the man’s hand.

“I can’t call you that while we fuck, that’s what I call my dad,” he said weakly, “Sorry.”

The man considered him for a moment.

“Your father makes you call him Sir?” he asked, sitting down next to Dean, not leaving much room between them.

“Sometimes,” Dean said, not turning to look at the man.

“Well that leaves us in a bit of a predicament,” the man said, a small frown on his face, “Because I like to be called ‘Sir’, you see. But if your daddy makes you call him ‘Sir’, then I guess I have no option but to make you call me daddy.”

“Like... Like ‘Daddy’ in a gay way, or are you gonna have me crawling around in diapers?” Dean asked, “Because I’m not shitting in my pants for you, dude.”

The man let out a soft laugh.

“No diapers,” he said gently, taking Dean’s chin in his hand and carefully studying his face, “It’s just a title. A way to uphold the dynamic between us, you being subservient to me, doing what I ask of you. You can do that, can’t you?”

“Yeah,” Dean said, a little lost in the man’s eyes.

The man tapped his cheek, an impression of a slap.

“That’s not how you speak to Daddy,” he said, his voice low and dangerous as he gripped Dean’s jaw again, tighter this time, “Try again. You can do what I ask of you, can’t you Dean?”

The tension in Dean’s body was unreal, he felt like he was on a precipice and the man was asking him to jump.

“Yes Daddy,” he said softly, not used to the words on his tongue.

“Good boy,” the man said, “Now that’s only for when we’re in private. If there are other employees around, you call me ‘Boss’, same as they do. Do you understand?”

“Yes, Daddy,” Dean said again, blushing at the words.

“Excellent,” Daddy said, shifting back to the ottoman across from him, “One last thing Dean, and then we can make this official.”

Dean waited, staring at his new boss.

“I want to see you naked.”

Dean wasn’t sure why it caught him so off-guard, the whole point of this arrangement was the idea that they’d be having sex. That this man, his new boss, Daddy, would be seeing him naked.

“Now,” Daddy said, his voice taking on a steely tone.

Dean nodded, slowly standing as though he was in a dream. His gaze shifted back to the windows.

“No,” Daddy said, “Look at me.”

Dean’s eyes snapped back down, focused on the man’s face. His fingers trembled a little as they pulled off his shirt, a plaid button up. He watched his boss watch him, dropping the shirt to the floor and grabbing the hem of his t-shirt.

He had his wits about him enough to try and make this sexy, subtly trailing his fingers across his stomach as he rucked the fabric up his chest, flexing his arms a little as he pulled it up over his head, wanting to impress his boss, to keep this opportunity. He may be a potentially dangerous loan shark but fuck if he wasn’t the hottest thing Dean had layed eyes on in months.

His hands dropped to unbuckle his belt, opening it slowly, his movements like molasses. His boss seemed to like it, his posture unchanged, but his eyes glued to Dean’s every movement. Like he was trying to appear unaffected. The hunger in his gaze gave him away.

Dean’s kneecaps may be at this man’s mercy, but in that moment, he felt powerful.

He eased his zipper down, so slowly it barely made a noise. Undressing like this, purposefully and methodical, had Dean hardening in his underwear. This became clear as he slid his jeans from his hips, revealing the burgeoning tent that was conveniently right at his boss’s eye level.

He toyed with the band of his boxer briefs, hesitating. Daddy pursed his lips a little, like he sensed it, his eyes fixed on Dean’s hands.

The message was clear: No stalling.

Dean took a deep breath, as quietly as possible. He slid his thumbs under the waistband, and pushed his underwear all the way down. It was a little chilly in the room, but his cock didn’t seem to notice, slowly getting harder as he stood there under Daddy’s sharp gaze.

“Turn,” was all Daddy said, assessing Dean’s body.

Dean stepped out of the puddle of pants at his feet, kicking them aside and out of his way, before slowly turning on the spot. He felt his skin prickle as though Daddy was touching him. He knew he had a nice ass, but he wanted to look over his shoulder, needing to see what Daddy thought, if he liked it.

“Touch yourself,” Daddy said, the second Dean was facing him again.

“Touch—?” Dean paused, his hand hovering next to his semi, uncertain.

Daddy nodded once, his eyes focused once again on Dean’s dick, waiting for him to take it in hand.

Dean did as he was bid, warm palm pressing against the smooth hot flesh of his cock, fingers circling his shaft as he started jacking himself, slow as ever. The slide was dry but Dean was sure that wouldn’t be a problem for long, pre-come already beading at the tip, just waiting to be smeared all over.

Daddy was still sitting on the ottoman in front of him, his face about a foot away from where Dean was stroking himself, the intense, burning gaze of his eyes focused on Dean and his ministrations. Dean couldn’t remember the last time he’d been this turned on. Daddy was looking at him like he wanted to devour Dean, and Dean was just about ready to let him.

“See anything you like?” Dean asked quietly, picking up the pace, so hard it hurt and dribbling pre-come all down his length. The glide was smooth and slick now, and Dean could feel the tension in his gut, the stirrings of an orgasm just beginning to build.

“Because this is just the interview, I’ll forgive you for not addressing me properly,” his boss said, eyes flicking up from Dean’s dick to give him a stern look, “Tomorrow, I expect you to be on top form.”

Dean’s stomach fluttered pleasantly at the way his boss spoke to him, helping him along. His hand sped up, his chest flushed prettily from the exertion of standing there and jerking off.

“Yes, Daddy,” he said, wanting to play the part, “I’m sorry.”

His boss merely kept watching him. Something about being so exposed, naked and masturbating in front of a fully dressed man, really had Dean going. Being watched, especially by Daddy... He liked it.

He started fucking into his fist in earnest, the pleasure really building now, looking down at his boss from under hooded lids, his lips open as he panted a little.

“That’s enough,” Daddy said.

“Wha—?” Dean’s hand slowed, but didn’t stop.

“Stop. Now,” Daddy continued, standing up, the heat of his body so close to Dean but not close enough, “I’ve seen all I needed to see. Get dressed please.”

Dean was kind of stunned. Thirty seconds ago, he’d been preparing for an orgasm and now Daddy wanted him to just... Put his clothes back on?

“I won’t ask again,” Daddy said, his voice quiet but dangerous, sharp like the blade of a well hidden dagger.

Dean nodded dumbly, stepping away from his boss to reach for his clothes, still piled on the floor. His brain was foggy with the need to come, his dick aching, begging him to keep going. He stumbled into his jeans and underwear, pulling them up at the same time, gently tucking his cock, still wet and slick, into his pants. He pulled on his shirts too, haphazard and distracted.

“Good boy,” his boss said, still watching him as he toed on his boots. “You may go. Someone will collect you first thing in the morning and bring you back here for some... Company onboarding. Try and get some sleep.”

Daddy showed him to the door, and before Dean knew it, he was in a different black Rolls Royce, being driven back to Milwaukee at nearly three in the morning. It wasn’t until he was at home, brushing his teeth in the bathroom, that he noticed he’d put both his shirts on inside out.

Dean felt like he was in deep shit.

**Notes for the Chapter:**

> Thanks for reading, I hope you liked what I have so far! Come find me on tumblr at mom-i-watch-gay-porn.tumblr.com !
> 
> I'm thinking about picking one person per chapter to get early access to the next chapter before it's posted, so if you're interested, make sure to leave a comment or message me on tumblr if you're interested. And leave a comment if you enjoyed this! Y'all know I crave validation.


	2. Company Onboarding

**Summary for the Chapter:**

> Dean and some co-workers getting ready for his first day on the job. 
> 
> There's not even any fuckin, im so sorry. pls forgiv me.

Dean was woken up at the crack of six-thirty by his phone ringing, loudly, on the mattress next to his head.

“‘Lo?” he mumbled, managing to answer the phone while keeping his eyes mostly shut.

“Hello to you too,” came the voice on the other end of the line. It was his boss—his other one, from the bar.

“Uh, hey Jerry,” Dean mumbled, sitting up straight, “What’s up?”

“I heard you walked off your shift last night, is that true?” Jerry asked, getting straight to business.

“Yeah, listen, I’m real sorry about that, I had a family emergency and I—,”

“I don’t give a shit, kid. This is a courtesy call to let you know your ass is fired. Don’t come back here again,” Jerry replied, before promptly hanging up.

Dean pulled the phone away from his ear and looked at it. That had taken barely thirty seconds. He sighed, tossing it to the side and just sitting there, thinking.

So he was fired from his real job, and his only income was soon to be from whatever this maniac in Chicago was going to have him doing.

Dean thought back to the previous night, blushing when he remembered the way his new Boss had watched him touch himself. He felt weird about it, and felt even weirder that his dick was onboard with the idea of seeing his new boss again today.

Daddy.

It sent a shiver down his spine and he wasn’t sure whether to be creeped out or not. It was a little different than jokingly asking ‘who’s your daddy?’, which wasn’t something he’d ever said anyway, because he wasn’t born in the forties. He sighed, resigning himself to the fact that it wasn’t like he had a choice.

He took his time in the shower, letting the warm water wake him up and soothe his tired body. He resolutely ignored his dick—he was mad at it, for getting so excited the previous evening, for making him look eager and easy. Not that he wasn’t eager and easy, he just didn’t like people to know it.

Especially not powerful, shady business men.

Dean had finished showering, put in a load of laundry, and was just doing one last wipe-down of the countertops by the time the knock came at his door.

He opened it, and there was Thick-neck, waiting on the other side. His neck looked a little thicker this morning. Dean wondered if he’d had any sleep—he’d barely got any himself, and yet Thick-neck looked as fresh as a body-building daisy.

“Come on, we’ve got appointments to get to,” Thick-neck said, in lieu of a greeting.

Dean nodded, and got ready to leave. He shoved his feet into his ratty old boots and grabbed his phone and his jacket, before gesturing for Thick-neck to lead the way. Thick-neck stayed where he was, hand out. Dean sighed, passing his phone over once again.

“What kind of appointments?” he finally asked, once they were on the interstate.

“Fucked if I know, I’m just driving your pansy ass around,” Thick-neck replied.

Dean mulled that over, gazing out the window. Snow was falling again, just a light dusting, typical of February in the Midwest. He didn’t bother talking again, focusing instead on the traffic. Thick-neck drove like a bully, cutting people off and tail gating. _What an asshole_ , Dean thought.

Eventually they were snaking through the streets of downtown Chicago, and Dean felt himself shrink down in his seat, despite the heavily tinted windows, as they passed a university building. He didn’t know if it was specifically Sam’s building, or if it even belonged to Sam’s school but shame curled in his gut all the same. He’d known straight away that he couldn’t tell his brother about this, about covering for their father yet again, about getting naked for money to cover for him, which was new.

They pulled up at the curb, outside an important and modern looking building.

“Out,” Thick-neck said.

Dean rolled his eyes, resisting the urge to flip the guy off as he stepped out of the car.

“Dean,” someone said, just to his left, and Dean turned to find Hannah.

She looked warmly dressed despite the cold, but her cheeks and the tip of her nose were a little pink despite her outfit.

“Sorry if we kept you,” Dean said, although there was nothing he could have done about it.

“It’s fine, you’re right on time,” Hannah said, gesturing for him to follow her inside.

“Where are we?” he asked, unzipping his jacket as they entered the nearly too-warm building, a huge white atrium with a rock garden and a giant snake plant by the reception desk. There was a fountain tinkling somewhere, but Dean couldn’t see it. The place felt sterile, bare of any personality or humanness.

“It’s a private clinic,” Hannah explained, bypassing reception entirely and heading to a bank of elevators off to the left.

“A clinic?” Dean asked, “What, am I getting a physical?”

Hannah just smiled at him.

Dean was right, as it turned out, he was getting a physical. And a full STD panel, which he felt stupid for not piecing together until the moment the doctor had his dick in hand.

After he’d been pronounced healthy and clean (some results pending), Hannah led him back downstairs, and out onto the street. Thick-neck pulled up just as they stepped out the door. These people moved like clockwork.

Hannah joined him in the backseat, pulling out her phone immediately.

“What else are we doing today?” Dean asked her, feeling out of his depth.

“We have a salon to go to, and then some fittings after that,” Hannah said, not looking up from whatever it was she was typing.

“A salon,” Dean said, “He wants my hair cut?”

“Not quite,” Hannah said, a wry smile on her face, never looking up from the screen.

Dean settled back into his seat and stared glumly out the window, watching the people on the street as they drove past. It was annoying not knowing what was going on, but in the long run it was better than smashed kneecaps. And an unexpected perk was getting to see a doctor for free, that was pretty great.

Soon enough he was being shown into another impersonal white reception area, except this one had a little white candle burning. Hannah walked right past reception again, like she’d been there a hundred times before. So far, they hadn’t had to check for appointments at all, everyone was just... Expecting them. Waiting for them to show up. Maybe it was good that Dean was going to be a boy-toy, he wasn’t sure he would ever be organized enough to personally assist anyone like his Boss.

“This is Helen, she’ll be taking care of your grooming today,” Hannah said, handing him off to a bored-looking middle aged woman in a pink apron.

“Grooming?” Dean asked, looking over his shoulder at Hannah as Helen pushed him down a hallway.

“In here,” Helen said, opening a plain white door to a small room with what looked like a kind of massage table. The space was filled with the overwhelming scent of lavender, and Dean felt like he might choke on it.

“Pants off,” Helen said, walking briskly over to a little station on the other side of the table.

“Excuse me?” Dean said, his voice a lot higher than he’d intended it to be.

“Pants off,” Helen said, turning her stiff gaze back to him, “I can’t wax you through your jeans,” she said, as though this was plainly obvious and Dean must be a little slow on the uptake.

Dean was at a loss for words. Helen looked mean though, and he’d made it this far already. He dropped his jeans with much less ceremony than he had the previous evening, covering himself with both hands as he stood awkwardly exposed in the corner.

“Up on the table,” Helen said, gesturing without looking.

Dean hesitated before approaching the table. He’d never been waxed before. Was she going to wax all of him, his chest, his legs? Or was this full brazillian territory? His cheeks burned as he imagined it. He’d been with girls before who were bare, and the soft smoothness had been nice against his own skin, his lips. He tried not to think about his new Boss’s mouth near his genitals as he climbed clumsily onto the table.

“Legs spread,” Helen ordered, pushing her little cart and a spinning stool over to the table. She sat down at the end, looking expectantly between Dean’s still-shut legs.

If Dean spread them, she was going to get an eyeful of his crown jewels. He really didn’t want this woman near his dick and balls but on the other hand, he enjoyed his kneecaps the way they were. There wasn’t really any other choice here; he took a deep breath and let his knees fall open.

“Hair’s not too bad,” Helen said, “Might need a quick buzz though.” She picked up a small pair of electric clippers and got to work.

It wasn’t awful, Dean thought. The clippers pulled at a pubic hair every now and then, and the quick, sharp pain was enough to stop him from getting hard as Helen gently moved his dick out of the way of wherever she was trimming.

Dean ate his words about five minutes later, just after Helen had smeared wax on his crotch and pressed the thin but strong looking muslin into it. She didn’t even count him down when she pulled the first strip off. The wax had been almost uncomfortably hot, but it was nothing compared to the burning as his pubic hair was ripped out of it’s follicles. Helen was a fucking sadist, repeating the process again and again, all around the base of his dick and all the folds of his sack. His eyes were watering, but he managed to only let out the occasional grunt as she tortured him methodically.

“Alright,” Helen said finally.

“Is it over?” Dean asked, his voice strained.

“Nope,” Helen answered, her tone awfully cheerful, “I need you up on your knees.”

Dean groaned. Up on his knees? What in the hell for?

He kneeled on the table, his crotch feeling puffy and sensitive.

“No, on your hands and knees. Turn around,” Helen said, and Dean’s heart sank.

She was going to wax his ass, he just knew it.

At least she was quick, swiping hot wax between his cheeks, which he had to hold open for her. He’d never felt more exposed in his life, and less than twelve hours ago he was jerking off in front of someone who could definitely kill him and get away with it.

“All done,” Helen said, finally, mercifully, and Dean felt like he might cry with relief.

She talked him through post-wax care, and pressed a bag full of lotions and scrubs into his hands.

“See you in six weeks,” she said airily as she pushed him back out into the hallway, as though that wasn’t the cruellest thing she’d said since they’d met.

“Ready to go?” Hannah asked, leaning gracefully against the front desk, tucking a wallet into her handbag.

“Yes,” Dean said, already done with today and wanting to go home and sleep.

“How are you feeling?” she said, as they stood in the elevator.

“Sore,” he replied, feeling grumpy and hyper-aware of his newly bare crotch.

“Well, we just have to go to the tailors, and then we can go back to the office,” Hannah said as they stepped into the foyer. Dean watched through the window as Thick-neck appeared, right on time.

The tailor was a breeze, compared to his morning. His underwear stayed on, and Hannah even brought him a chicken sandwich before sequestering herself on a plush sofa in the corner.

The head tailor, Mr. Flack, measured him all over. His shoulders, his back, the width and breadth of his chest. How long his legs were, how fat his ass was. He called the measurements out to his twiggy little assistant that Dean couldn’t remember the name of, and Dean just stood there on the fitting podium in his socks with his arms out to either side.

They were just in the process of stuffing him into a dressing room with some sample suits to try on, when the bell above the front door chimed.

“Hello Hannah. Where is he?”

Dean felt his gut clench, faltering slightly as he eased the suit pants up over his hips. His new Boss’s voice was deeper than he remembered, kind of gravelly, and Dean strained to hear more of it through the thick curtain.

He didn’t have to strain for long, because the fabric twitched slightly, and before he knew what was happening, his Boss was in the cozy dressing room with him.

“Good afternoon, Dean,” his Boss said, his eyes just as intense as Dean remembered.

“Hello,” Dean said, and then, more quietly, “Daddy.”

His Boss had a great smile, Dean noticed, watching as it spread across the man’s face at his greeting.

“How are you today?” his Boss asked.

“Um, I’m fine,” Dean said, chewing his lip a little, trying not to meet the gaze being levelled at him right that minute.

“Just fine?” Daddy asked, placing his hands lightly on Dean’s hips, just over where his suit pants sat, pulled up but not buttoned.

“Well, I did get my balls waxed, so that wasn’t exactly fun.” Dean replied, stiff in Daddy’s arms, “I didn’t think you’d be the type to like the completely bald look.”

“Oh? You've been thinking about what I might like?” Daddy asked, his thumbs rubbing soothing circles against Dean’s sides.

“No,” Dean said, his voice small, “I just meant, you know, yesterday you said this wasn’t a weird baby thing, but it sure feels like it might be.”

Daddy smiled at him, hands tightening on his hips.

“If it was a weird baby thing, you’d still do what I asked of you and thank me for the honor. But I assure you, it’s purely perfunctory,” Daddy leaned in, his lips brushing Dean’s ear as he whispered, “Trust me, you’ll be grateful for it later when you’re not combing dried come out of your pubic hair.”

Dean blushed at the words, sure that Daddy could feel the heat radiating from his cheeks.

“Okay,” was all he managed to say, not meeting Daddy’s eye.

“I want to see,” Daddy said, easing his fingers under the waistband of Dean’s suit pants.

“I—,” Dean was hyper aware of his reddened, sensitive crotch, “Helen—the waxer, she said not to touch the skin while it was inflamed, or it could get, uh, an ingrown hair or something.”

Daddy looked down between their bodies, at where Dean’s snail trail disappeared into his underwear.

“Well I wouldn’t want to spoil your lovely skin, and I’m not sure that I could look without touching right now. I’ll just have to unwrap you next time, like a present.”

Dean nodded, thankful that his Boss had backed off.

“And are you being a good boy?” Daddy said then, taking Dean’s hands in his own.

“I—Yes?” Dean answered, unsure of how he could have misbehaved, before hastily continuing, “uh, Daddy.”

“Good,” Daddy said, “I’ll see you later then.”

He brought one of Dean’s hands up to his mouth, pressing soft, warm lips against Dean’s knuckles, before he slipped back through the curtain. Dean stood there, half dressed and stunned, until he heard the bell above the front door tinkle again. He slowly pulled on his dress shirt, unsure of what in the hell just happened.

“So,” Hannah said, once they were back in the car with Thick-neck a few hours later, “We’re going to get you some nice suits made, so that if you need to accompany the Boss anywhere, you can do so while dressed appropriately. I’ve already sent your measurements and sizes off to our shopper, so they can purchase all the clothes that the Boss requested for you in the right sizes.”

“All the clothes?” Dean repeated in question, “Is there a uniform or something?”

“Well,” Hannah said delicately, clearing her throat a little, “There are a number of specific things that the Boss has specified he would like to see you in, so we want to have them all on hand and ready for you to wear if he asks.”

“Oh,” Dean said, not wanting to think about what that could mean.

“There’s a wardrobe for you in his quarters with a powder room included, which will be fitted out with all your new items.” she tucked a piece of hair behind her ear and carried on, “We’ll put your skin care products in the adjoining bathroom, which will be just for you to use. He feels it’s important that his staff have a sense of personal space while at work, considering how demanding our jobs can sometimes be.”

“How kind of him,” Dean said, keeping his tone light and neutral.

“Yes,” Hannah smiled, seemingly pleased at Dean’s attitude, “Despite the circumstances surrounding your employment, he’s always made sure to treat us well. I’m sure that will include you.”

“That’s good to know,” Dean replied, remembering that this weird day had been the ‘company onboarding’ that their Boss had mentioned. He’d never had a brazillian be a job requirement before, but there was a first time for everything.

The sun had just begun to set as they pulled up to the same office building as the previous night. Even with the fading light of a winter afternoon, Dean could now see the small discreet signage outside the parking garage. Genesis Enterprises. That’s what Thick-neck had said too, at the bar. He made a note to look it up later, when he got home.

Hannah ushered him through the heavy wooden doors of their Boss’s quarters, and Dean felt his cheeks heat up again as he saw the white sofa where he’d exposed himself the previous evening.

Luckily for him, Hannah led him the other direction, to the far end of the large apartment, and into a spacious office room. There were bookshelves lining the walls, a well-stocked liquor cabinet, and a big, imposing desk sitting in front of the floor-to-ceiling windows. The room had dark wood panelling, with deep earth toned wall-paper. It felt like a very masculine space to be in, so Dean wasn’t surprised to see their Boss sitting at the big imposing desk, looking very much like this was exactly where he belonged.

“Ah, Hannah,” their Boss said, “Thank you for looking after him today.”

“It was my pleasure,” Hannah said, nodding her head once before leaving the room.

Meaning that Dean was alone with the Boss again.

“Please, take a seat, Dean,” his Boss said, gesturing to a chair on the other side of the large desk.

Dean sat, hands in his lap, as he watched his Boss tidy up some folders.

“I have an employment contract to go over with you,” his Boss said, passing what looked like a copy of the document across the desk to Dean. “You’re expected to work five days a week, but you will also be on call. So if I have you here Monday to Friday, but I want you to come in on Saturday and Sunday too, you will come in, is that clear?”

“Yes Daddy,” Dean nodded, scanning over the first page of the contract.

“Good. You will also start at nine o’clock, and stay here until dismissed. If that means ten, twelve, sixteen hours days, then so be it. I don’t employ slackers.”

Dean nodded, agreeing only because sixteen hours on his back was bound to be less physically demanding than sixteen hours tending bar.

“How much were you paid previously?” his Boss asked, looking down at the contract.

“I was on minimum wage,” Dean stated, “Plus tips. ...Daddy.”

“Perfect,” his Boss said, making a note on the contract, “You’ll be fine carrying on with that then.”

“Hang on,” Dean said hurriedly, “Don’t sex workers make, like, really good money?”

His Boss smiled at him.

“Sure, but usually they’re self employed and can set their own rates. You’re paying back a debt, and therefore work at the rate that I set for you.”

“So... I’m sucking dick for eight twenty-five an hour?” Dean asked, not quite believing what he was hearing.

“Plus tips,” his Boss said with an air of innocence, as though this was a reasonable situation to put Dean in.

“And how much are you taking out of that to repay my father’s loan?” Dean said, frowning.

“Well, all of it,” his Boss replied, “We’ll take the eight twenty-five, you can keep whatever tips you make.”

Dean gaped at him.

“And how much would that be? How am I supposed to pay my rent?” he asked incredulously, “I need to help my brother get groceries!”

“That doesn’t sound like my problem,” his Boss said, frowning back at him.

“Are you fucking kidding me?” Dean said, “You got me fired from my job because your goons hauled me away in the middle of a shift. You’re threatening me and my little brother. You send me to get my asshole waxed instead of spending all this time and money and manpower on finding the person who actually took out the loan in the first place. This is your fault, and it sure as hell is your problem.”

His Boss considered him for a moment, his gaze cold as he processed what Dean had all but shouted at him.

“Your father, your family, borrowed money from one of my subsidiaries, a member of my family,” his Boss finally said, “He was given four months to begin scheduled payments, all of which he missed. That means that the debt comes back to me to collect, in the same way it comes back to you to pay.”

“That’s not how the law works,” Dean said weakly, desperately trying to make the man across from him see sense.

His Boss stood then, and walked around the desk to stand next to him, grabbing Dean’s chin and forcing him to crane his neck to make eye-contact.

“I don’t give a fuck how the law works, Dean,” his voice soft but clearly dangerous, “Your family owes my family, and this is how it is, no matter how much you wish it weren’t. Take your lot and be grateful I’m being this lenient with you. Figure out your shit.”

He tightened his hold on Dean’s chin, staring intently down at him. He almost looked unhinged, and suddenly Dean understood exactly why this man was as rich and powerful as he was.

“And you’ve forgotten to address me properly all but once, so we’re going to have to do something about that.”

Dean closed his eyes, cursing himself. He was in too deep to back out now.

“I’m sorry Daddy,” he grit out, his whole body tense “It won’t happen again.”

“It better not,” his Boss said, finally letting go of his chin, “Let’s get this contract signed, we’ll deal with your bad behaviour tomorrow.”

Dean nodded stiffly, accepting the pen his Boss passed him, and signing his life away on all the appropriate dotted lines.

“Can I ask something?” he said, handing the signed document back to his Boss, who just raised his eyebrows, waiting for the query.

“Will I be allowed my phone? I need to be available to my brother, just in case,” Dean explained, hoping that his Boss would be merciful after his little outburst.

He watched as his Boss considered him for a moment.

“I’m sure you understand that I value my privacy, Dean,” he started, “You may have your phone on, and charged, but you will only be permitted to use it to check and reply to any messages from your brother at set intervals throughout the day. You will be supervised. Keep the sound on, and you can answer your brother if he calls. Otherwise, the phone is off-limits.”

“Thank you,” Dean said, letting out the breath he’d been holding, “Daddy,” he added hastily, not wanting to make tomorrow any worse.

“Good. Well, we’re settled then. That will be all. Someone will meet you at the front door to escort you home,” his Boss said, turning back to the papers on his desk and not sparing Dean another glance as he dismissed him, “I’ll see you tomorrow at eight for breakfast.”

Dean nodded, not that his Boss saw him, and turned to leave.

“Dean,” his Boss called after him, his tone slightly softer than it had been a minute ago, “As long as you work for me, you’re under my care. That means something around here.”

“Okay,” Dean said, standing awkwardly halfway across the room, just far enough that he couldn’t quite make out the look on his Boss’s face, “Thank you, Daddy.”

“You’re welcome,” his Boss said, turning back to his work.

Dean let himself out the front door, where a different Thick-necked man was waiting, holding Dean’s phone. He didn’t get it back until they were three blocks away from the office.

During the car ride home (and the considerable time spent sitting in traffic), Dean messaged Sam, trying to catch him up on the situation without telling him much more than the bare essentials.

_< < Hey man, got a new job. Gonna be some schedule changes._

_> > cool! Better pay?_

_< < nah, but there are some pretty good perks. Free meals being the main one._

_> > lol. What are your days off?_

_< < weekends. But I’m kinda on call so I may have to up n leave if we’re hangin out_

_> > oh shit thats intense. What kind of bar needs a bartender on call??_

_< < it’s just a bit more responsibility. If someone calls in sick, or there’s some kinda fuckup, i gotta go in and fix the problem, stuff like that._

_> > damn. you’d think they’d pay you more._

_< < you’d think!_

_> > well anyway, thats really cool. Proud of you!_

_< < thanks :)_

_> > :p_

Dean collapsed on the sofa the minute he got in the front door, right next to the mostly empty laundry basket that his father had been ransacking earlier that week. In it was a ratty pair of jeans and a few odd socks. Dean sighed and pushed the basket onto the floor, so he could stretch out along the couch.

He thought back to what his Boss had said about his wages, and how they supposedly included tips. Maybe if Dean made enough extra he could scrape together rent. He could reduce his bills to almost nothing if he ate and showered exclusively at the office. It would suck, but it could work. And really, if the power got shut off it would be more help than hindrance.

He looked at his phone again, thinking about his brother. Sam always said he was fine without any extra money, but Dean knew it made his life a little easier. Now that he was essentially an indentured sugar baby, he was going to have to play the part as best he could to ensure that his Boss felt like being a generous tipper.

He googled ‘Genesis Enterprises’, but only found some bullshit landing page with generic stock images and a mission statement that was potentially the vaguest thing Dean had ever read. There was no information on who worked for the company, or any contact details. It was clearly a decoy page, and a decoy company name.

None of that really mattered though, because it all came back to this: He still had rent to pay. Rent on a stupid two bedroom apartment for one only person, because his father had a knack for setting him up for failure. He’d take care of that first, and figure the rest out afterwards.

He could sell some stuff, he supposed. Not his car—never the car, but he had a few things lying around that he could do without. Like the television, or whichever kitchen appliances weren’t nailed down, if it came to that.

It would be difficult. But, then and there, Dean resolved to get through this as best he could. He’d be damned if he let John ruin his life again.

**Notes for the Chapter:**

> im on tumblr at mom-i-watch-gay-porn ! 
> 
> I didn't do an Advanced Reader Copy for this chapter bc it's not even sexy, but Chapter Three will have an ARC so! lemme know if ur interested and I'll pick someone to share it with once it's written.


	3. Relief and Regret

**Summary for the Chapter:**

> Dean's first official day on the job. 
> 
> I got a little carried away describing Dean's powder room area, so feel free to skip the first little bit if you aren't at all interested lmao. No hard feelings!

It seemed like his Boss had an infinite supply of thick-necked men to drive Dean around. Or maybe the one on Thursday morning was one of the ones he’d already met? Dean wasn’t entirely sure, they all looked the same.

They all behaved the same, too. Ushering him into a black SUV and ignoring him for the entire drive to Chicago. Hannah met him at the elevator, leading him in and pushing the button for the forty-ninth floor. She was on her phone again, tapping furiously at the screen as she blindly led Dean down the hall and through the Door’s of their boss’s residence.  
“Okay,” she said, finally looking up once they were standing in the middle of the foyer, “I can’t give you a full tour right now because I have a few things to do, but go ahead and take a quick look at your personal rooms before the Boss gets here.”

Hannah indicated a door to his left, which blended in with the wall so well he hadn’t noticed it either of the times he’d previously been in the office apartment. He turned the handle gently and pushed, the door swinging silently inwards as he did so.

It really was a beautiful room. White walls and the kind of lighting that seemed to come for everywhere all at once. Next to the door, there was a vanity with a large mirror and what looked like a dozen different skin care items arranged neatly on the surface. Across from the vanity was a plush looking chaise lounge, a deep navy blue, with blush pink throw pillows and a fluffy white blanket. There was a small coat stand with a shelf, tucked away into the corner for what Dean assumed were the clothes he was wearing.

There was a door directly across from him, between the vanity and the sofa. To his right, was an archway leading to the biggest wardrobe Dean had ever seen. There were drawers and shelves and rows of hangers. There was a floor length mirror, presumably for him to stare at himself as he got dressed in whatever his Boss had requested to see him in.

He left that for later, instead choosing to open the other door off the powder room, pushing it open to reveal what was probably the most luxurious bathroom he’d ever seen in his life. He could tell it was expensive, because the tile on the floor was so small and white, shaped like little hexagons.

A huge bathtub with jets took up most of the far wall. There was a walk-in shower with glass walls and a small wooden bench. The sink was incredible, large and rectangular, set into a big marble countertop with gleaming copper fixtures. He could see the lotions and scrubs Helen had given him the day before all lined up on the counter, ready for him to keep his skin smooth and soft and inviting.

“This sure is something,” he said to Hannah as he left the bathroom, noticing her leaning against the doorframe to the powder room.

“Yes,” Hannah replied, “It’s an area just for you, a place to go when the Boss is busy and you need some downtime.”

“It’s—I don’t even know what to say, to be honest,” he said, shoving his hands awkwardly in his pockets.

“It can be like that at first,” Hannah said, “I’ll leave you to it. The only instruction I have to pass on is that you should change into fresh clothes, otherwise you’re free to do what you like. The Boss will be down at eight to have his breakfast with you.” She turned and left, already focusing on her phone again.

Eight o’clock meant he had ten minutes to pick something out, preferably something comfortable. There was a wall of closets, filled to the brim with suits; business casual, three-piece, a tuxedo. Dean considered showing up to breakfast in a tux, but figured his boss probably wouldn’t appreciate the humour in it. He tried the opposite wall, which was almost entirely drawers. He found soft, folded fabrics, cotton t-shirts and jersey lounge pants.

He opened one of the drawers closer to the archway and felt himself freeze.

Underwear. Women’s underwear. Silk and lace and satin, all colours and cuts. They were in his wardrobe, so they must be for him. He opened all the other drawers as quickly as he could, but the panties were the only underwear he could find. It was them or nothing.

The closest he could find to his own underwear was a pair of low-cut briefs, made of a soft jersey cotton, black with a lacy trim on the legs. He looked in one of the full length mirrors, grimacing at the way his ass cheeks hung out, hugged closely by the fabric. There was going to be no hiding in these. They did feel incredible against his smooth, waxed skin though.

He slid on a pair of lounge pants and a t-shirt, both soft cotton that felt more expensive than anything he’d ever worn before.

He stepped back into the foyer at two minutes to eight, the marble tile cold on his bare feet. He had no idea where the dining room was so he just sat and waited on the low padded bench that was pushed against the wall beside his door.

The front doors creaked open at exactly eight o’clock, and in walked his boss.

“Good morning, Dean,” he said, not stopping to chat, “Follow me please. It’s time for breakfast.”

Dean followed him, down the other hallway and into a room with huge windows. It was softly lit, and beyond that Dean could see the shell-pink colour of the sky as dawn broke.

The table was big enough to seat eight people, and his boss sat at the head of it. Dean hovered.

“Next to me please,” his boss said, gesturing to the seat on his right. Good, Dean thought, at least he wouldn’t have to look out the window from this god-awful height while they ate.

As soon as he sat down, a service door opened somewhere behind him, and a man dressed as a waiter stepped smoothly into the room.

“Good morning, Sir,” he greeted, moving to pour their boss a tall glass of ice water, “What can I get for you?”

“The usual please, Isaiah,” the boss said, taking the newspaper that the waiter—Isaiah, handed him.

“And for your guest?”

A glass of ice water was placed in front of him.

“Whatever he wants,” Boss said, already reading the newspaper.

“Sir?” Isaiah turned to him then, waiting with his hands behind his back.

“I, uh,” Dean floundered, “I don’t know. Is there a menu or something?”

“Whatever you feel like eating, we can get for you,” Isaiah smiled at him, “Anything at all.”

“Wow,” Dean said, shifting in his seat, not sure what to do other than to follow his stomach’s orders, “Waffles, I guess. With, uh, syrup. And chocolate chips. And berries on top. And some bacon and eggs. Eggs over-easy. And a big coffee.”

“Of course,” Isaiah said, motioning to move back through the door.

“And some mimosa’s please,” Boss added on, “We’re celebrating this morning.”

“What are we celebrating, Boss?” Dean asked, aware that Isaiah was still in the room.

“Your new job,” his boss replied, smiling over the top of his newspaper, “Congratulations.”

Dean laughed nervously, a small huffing sound as he sat there in his new clothes, in this ridiculously expensive room, with a man who could kill him and make it look like a tragic accident.

They sat in silence, the room so still aside from the gentle rustle of pages moving, that it took a few minutes for Dean to notice that there was soft jazz playing, audible enough to fill the quiet room but not loud enough to be intrusive. Or noticeable, even.

The service door clicked again, and Isaiah walked in, pushing a big silver food cart in front of him, laden with their breakfast. The boss was served first; granola and yoghurt, fresh fruit salad, a small, steaming teapot, and a plate of crispy bacon.

It wasn’t what Dean expected, but then he supposed he wasn’t really sure what crime lords were supposed to eat for breakfast.

“So,” his Boss said, once they were alone again, “What do you think your punishment should be?”

Dean faltered, his mouth full of waffle, trying to swallow it quickly so he could answer.

“My punishment?” he asked, reaching for his mimosa. Fuck that was some fresh orange juice.

“For being belligerent with me yesterday,” his boss said, watching Dean closely.

“Oh,” fuck, he’d forgotten about that, “What do you think it should be?”

“I know what I think, I want to hear what you think,” his boss replied calmly.

“Oh,” Dean said again, “Uh... Honestly, I’m not sure what to expect. I’m guessing a time-out is off the cards?”

“I could organize a time-out,” his boss said, musing it over, “But it would be slightly different than what you’re probably thinking.

Right. The reason he was here.

“A sexy time-out,” Dean offered, taking another sip of his ridiculously good mimosa.

“Yes,” his boss smiled a little, his eyes twinkling with it, “It would be sexual in nature.”

Dean breathed out at that, not sure what to do with himself.

“Seeing as it’s your first day, I’ll just tell you what we’re going to do,” the Boss said, taking mercy on him, “We’re going to finish our breakfast, and once the plates are all cleared away, I’m going to bend you over this table and spank you until I feel that you’ve truly learned your lesson.”

Fuck, oh god. Dean chubbed up just thinking about it, the strength his boss would be able to put into each swing with his thick, muscular arms.

“Okay,” Dean said, swallowing down his arousal and panic.

“Good,” the Boss said, turning back to his food, reading the newspaper as though what he’d just said was entirely normal.

Dean could barely focus on what he was doing, shoveling food into his mouth just to keep himself from over-thinking their conversation. His whole body was tense with anticipation, but fear thrummed through him too, unsure as to how far this handsome maniac would take things. Maybe he was about to be in for a world of hurt. There was no way of knowing.

Soon enough, they were both finished, and Isaiah was pushing the silver cart with all their empty dishes back through the service door. It swung shut, and they were alone.

“Come here, Dean,” his Boss said, pushing his own chair back from the table.

Dean stood, a little shaky on his feet, and moved over to where his Boss still sat.

“Well,” Boss said, gesturing at the table in front of him.

Dean took his place, tentatively glancing over his shoulder to make sure he was doing it right, before lowering his chest down against the wood in front of him, braced a little on his forearms, his ass basically in his Boss’ face.

It was dead quiet, the newspaper and the smooth jazz long-since abandoned. Dean could hear his own breathing, his heartbeat, both loud inside his body. He felt his boss, nudging his legs wider with one knee. He felt warm skin along his lower back, and then his lounge pants were tugged down over his butt in one swift movement.

“Hmm,” he heard from behind him, “These were a safe choice. Pretty, obviously. But safe all the same.” The waistband of his panties was pulled on and then snapped back against his skin, emphasising the point.

Then they were pulled down too, and Dean’s ass was bare, and his Boss was tracing a finger along the crease where his cheek met his thigh.

“You really are lovely,” his boss said, rubbing firmly over his cheeks, grabbing a handful of his ass and squeezing.

“Thank you,” Dean said, trying to keep his manners.

He yelped in surprise as a sharp slap landed against his cheek.

“Not addressing me properly is a sign of disrespect, Dean,” his Boss said, pinching the flesh of his inner thigh until he squirmed, “Do you really think it’s a good idea to disrespect me?”

“No, I’m sorry,” Dean said, breathing harder from the pain, “I’ll uh, I’ll try harder Daddy, I promise.”

“Good boy,” his boss—Daddy, said, rubbing a soothing hand of the stinging spot on his thigh, “I’m going to help you keep your promise, by making sure you don’t forget.”

Another sharp slap rang out, piercing the stillness of the room, and Dean gasped again. Daddy was not pulling his punches, not in the slightest. Another blow came, and Dean lurched forward, clinging onto the table for dear life, his cock trapped between his body and the wood beneath him.

He lost count pretty quickly as his Daddy laid a few particularly hard blows to his upper thighs, nailing him right across the balls. The pain was sharp and he couldn’t think properly. It stung so bad, and he felt winded, but Daddy didn’t stop. His ass was burning, like the skin was pulled too tight across his muscles, like the heat in his face as he blushed. Every now and again, Daddy would stop and use a soothing hand to massage his hot skin, a tender and gentle touch sandwiched between periods of what felt like unending pain.

He only noticed that he was hard when his dick started sliding through a puddle of pre-come that must have dribbled out at some point. And fuck, this was kind of hot, wasn’t it?

It felt good, to be touched, not only gently but at all, by firm hands that delivered pain which had crossed over into pleasure. The stinging started to feel good. Dean's eyes were watering but he wanted more.

Just as he reached that realization, the blows slowed to a stop.

“There,” Daddy said, sounding a little breathless, “Do you have anything to say for yourself?”

“Thank you,” Dean croaked out, “For helping me remember, Daddy. I won’t forget again.”

“Good boy,” Daddy said, easing his panties back in place and helping him stand up straight, “You’re forgiven.”

Dean felt stiff, his back sore from bending over.

“Oh dear,” Daddy said, his voice a murmur near Dean’s ear, “You seem to have made a mess on my nice table.”

Dean followed Daddy’s line of sight, landing on the spot of pre-come he’d drooled on the polished surface.

“Sorry Daddy,” he murmured back, feeling his cheeks flush harder as his cock throbbed at the sight of it.

“You’d better clean that up before Isaiah sees it.” Daddy said, grabbing Dean by the neck and pushing his face towards the table, “He won’t be too happy if you leave that from him to find.”  
Dean’s head felt fuzzy, but he bent over again at his Daddy’s will, until the tip of his nose touched the sticky wetness.

He couldn’t recall if he’d ever been this hard in his life.

“Don’t keep me waiting,” Daddy said, the grip on his neck tightening.

Dean felt his cheeks flame as he stuck his tongue out, licking through the puddle on the table-top, licking at the wood in earnest, lapping up every drop until the only thing left was his spit.

His cock ached.

He heard a slick noise behind him, but his face was still pressed against the table. There was a grunt, and then a warm splash across his jaw.

“Looks like you missed a spot,” Daddy said, his voice raw.

Dean was glad his panties were covering his dick as he felt more precome drool from the tip. It had got him into enough trouble as it was. His own breathing felt ragged as he moved his face, his mouth brushing the streak of semen, letting it smear across his lips before he started licking it up in earnest. It was salty and cooling off, which made him work quickly, wanting to get it while it was hot, as it were.

“God, look at you,” Daddy muttered, stroking his neck while he worked.

It didn’t take long, and then he swiped the come off his chin and slowly sucked it from his fingers, still bent over and still hard in his pants.

“Good,” Daddy said, once he’d finished, letting him stand up straight again, “I have to do some work now. Let’s go.”

He pointedly kicked Dean’s lounge pants to the side, before leading him out of the room with one hand still holding tight to the back of his neck. Dean felt exposed, walking through the apartment in a pair of women’s panties with a raging erection, but it wasn’t like anyone was going to see him, he supposed.

They came to Daddy’s office, and Dean was pushed down onto a leather chaise lounge, tucked into a corner of the room where Daddy could still see him.

“You can do whatever you want, read a book, have a nap, I don’t care, but don’t disturb me while I work.”

“Yes Daddy,” Dean said, shifting onto his side to ease the burn from sitting on his freshly-spanked ass.

“Roll over, I want to see you.”

Dean did as he was bid, shifting onto his stomach so that Daddy could look at his red and stinging cheeks, his erection waning from lack of stimulation. The couch was comfortable. There was a fluffy cushion under his head, and soon he was drifting off.

He woke up to a room cast in long shadows, and a cool hand against his aching flesh.

“Hello,” came Daddy’s voice, gentle and close behind him.

“Hi Daddy,” Dean said, his voice rough from sleep, “Did I sleep too long?”

“No, you needed it, I suspect. You had a strenuous morning,” Daddy said, massaging something soft into his burning skin, “I would have let you sleep, but I felt compelled to apply lotion to your rear. It looked sore.”

“Mm, it is a bit. But in a nice way,” Dean said, relaxing into the strong hands on his skin, chubbing up a little as Daddy pushed his panties up out of the way, the fabric pulled tight between his cheeks, cupping his package in a particularly pleasant way.

“You enjoyed your punishment?” Daddy asked, his voice teasing.

“You know I did,” Dean said, pushing back into Daddy’s hands, enjoying the soothing touch.

“Well we might have to amend any future punishments. You won’t learn anything if you’re having a good time.”

“Mmm, I don’t know about that, Daddy,” Dean moaned a little as Daddy worked him over, spreading his cheeks a little to run his thumbs along his crack where the panties were resting, “I think the lesson has been seared into my brain.”

“Really?” Daddy said, “Well then, I think my lovely boy deserves a reward for being such a quick learner.”

Dean felt Daddy shift behind him, and then hands were tugging at his panties, pulling them down and off his legs.

“On your knees,” Dadd murmured, tapping Dean’s hip.

Dean got his knees under him, his ass exposed while his head and chest stayed pressed into the leather beneath him.

Hands were on him again, spreading his ass apart, and then he felt soft gentle kisses along his crack, the smoothness of his freshly waxed skin enhancing every touch.

He’d been eaten out once, years and years ago, by a girl he’d been seeing at the time. She had talked him into it, but had been timid, giggling as she kitten-licked at him. It had felt nice, but soon enough her curiosity waned and they’d moved on to something else.

This though, this was different. Daddy’s tongue was like magic, flicking gently along his rim, swirling against him and then pressing against his hole, wet and slippery tongue spearing into him. Dean had been sleepy and relaxed, but soon he was strung tight, desperate for more, pressing his ass back against his Daddy’s mouth as Daddy licked him open, moaning against Dean’s hole like he was the one being pleasured.

Dean was hard again, his cock back to its old tricks, a thin line of pre-come dripping down onto the leather beneath him. He felt a finger pressing against his rim. Soon enough it was two, and then Daddy was pressing and curling his fingers inside Dean, his mouth moving down to kiss and lick Dean’s sac as it hung heavy between his legs. Dean’s hands clenched, grabbing at the cushion in front of him, the waves of pleasure rolling through him as Daddy pressed all his buttons.

“Jerk yourself off,” Daddy said, his voice low and commanding, rough from what Dean hoped was desire.

Dean got one arm under him and on his dick lightening fast, fucking into his fist and back on Daddy’s fingers. It felt incredible, and the tingle at the base of his spine started up, spiralling through him slowly until he felt Daddy suck one of his balls into his mouth, rolling it gently across his tongue, and that was all it took before he was spilling hot and fast over the leather.

“Fuck,” he panted, head resting against his forearm as the fingers in his ass slowed.

“Good boy,” Daddy said, leaning heavy across his back.

Dean remembered his come, and wiping it up with his hand before licking it off his fingers, wanting to do it now before it was cold and disgusting.

“Fuck,” Daddy said, “Dean, that was—.”

He cut himself off, and then Dean felt the blunt head of a cock pressing against his thighs. Daddy pushed his legs together, and Dean took the hint, squeezing his thighs as much as he could as Daddy started to fuck the hot, wet space between his legs, cock head nudging his balls every now and then. Dean pushed back into it, hoping to make it feel good for his Daddy, wanting to please him.

Soon enough Daddy’s hips stuttered to a stop and Dean felt come spread hot and thick behind his balls. He thought of what Daddy had said about combing it out of his pubes and was suddenly very grateful that he’d been waxed clean.

“Do I have to clean that up too?” Dean asked, mostly joking.

“As hot as that would be, you’ve been such a good boy that I think I’ll help you out,” Daddy said, lifting Dean’s hips again and moving in, licking Dean’s skin clean of his spend. He had to roll Dean over and press his thighs up against his chest to get to the tricky spots behind his balls, but he got them all, finally surfacing from between Dean’s legs with pink lips, spit-slick and swollen.

Dean pulled at his shoulders, until Daddy was laying on top of him, their bodies pressed together tightly. He kissed Daddy’s neck, laving his tongue over the skin there until Daddy took him by the jaw and forced him to meet his mouth. Dean felt a thrill run through him as he tasted himself on Daddy’s tongue, salty and tart.

The kiss was messy, and so hot that if Dean hadn’t just come, he’d have been hard in an instant. They spent a while on the sofa, making out and just touching each other, until Daddy’s cell phone dinged, the noise ringing out in the quiet of the office from where it sat on Daddy’s desk.

Daddy sighed against Dean’s mouth, kissing him one last time before getting up and checking his message.

“Listen, I have some work to do, and then I have to go out for a few meetings. I won’t be back until late. If you stay here, I’ll never get anything done.”

“Okay,” Dean said, watching as Daddy came back over to him.

“I want you to wear these home,” Daddy said, retrieving Dean’s panties from the floor.

Dean slid them back on, up over his thighs and ass, tucking his junk in at the front until he was comfortable.

“Go get changed, I’ll meet you in the foyer.” Daddy said, pressing a soft kiss to his cheek.

Dean wandered back to his rooms, feeling a little dazed as he got dressed again, swapping the expensive new t-shirt for his old, thread-bare one.

Daddy was waiting for him by the door when he stepped out of his room, frowning at his phone.  
Dean stood quietly next to him, his own phone burning a hole in his pocket.

“Sorry to keep you,” Daddy finally said, putting his phone away and pulling Dean against him, “You were so good today.”

He pressed his lips to Dean’s, insistent and searing hot. Dean squeaked into his mouth as Daddy hauled him closer by grabbing his ass and squeezing it, fingers digging into the inflamed flesh beneath thin denim.

“I’ll see you tomorrow,” he said, fiddling with the waist of Dean’s jeans, like he couldn’t decide if he wanted to cop one last feel.

“Bye Daddy,” Dean replied, batting his lashes a little, playing up the kept-boy act a little.

“Bye,” Daddy said, giving him one last sharp swat to the rear before pushing him out the door.

There was a goon leaning against the opposite wall, who started walking off the second the door clicked shut, not bothering to wait for Dean.

“Hurry up,” he said over his shoulder, “I don’t wait around for pansies.”

Dean rolled his eyes, but jogged to catch up.

He got home by six, his apartment cold and empty. Dean sighed, deciding to have a hot shower before parking himself in front of the T.V. for the rest of the evening.

It wasn’t until he was in the bathroom, easing the soft panties down over his aching ass, that he noticed the bills. Three crisp benjamins fluttered to the floor, laying innocuously on his ratty, stained bath mat.

Daddy must have tucked them into his panties just before he left. That was a four hundred per cent tip.

Dean’s shoulders sagged, and he slid down the bathroom wall until he was sitting opposite the bath mat that had more money that was currently in his bank account. He let the relief wash through him, feeling a strong urge to cry, and maybe punch something. Daddy—no, his Boss, Dean reminded himself, his Boss had taken care of him, but he’d also let Dean think he’d be on his knees for minimum wage.

Dean got up abruptly, overwhelmed with the urge to brush his teeth, his tongue, any part of him that had willingly and eagerly come in contact with that maniac’s jizz. His cheeks burned with shame, even though he was alone in his bathroom, and no one knew what he’d done.

At least he could pay his rent, he reminded himself as he tried to scrub himself clean under the hot spray of the shower. His water pressure was shit, and the shower head was too low on the wall for someone as tall as him. The water pressure in the Genesis Enterprises building was probably incredible, he thought bitterly.

He rolled into bed, tired and worn down, wanting to just sleep off the day and the wave of shame he’d felt when he found his day’s “tips”.

And worse still, he had to go back tomorrow. He badly wanted to call his father and curse him out, but he knew John wouldn’t answer.

The most gutting part though, so embarrassing he could hardly bear to think about it, was how Dean’s stomach flipped over every time he remembered the way his Boss had touched him, kissed him, licked his skin, and pressed himself down on top of Dean.

He woke up the next morning to a shrill alarm and the hardest morning wood he’d had in years.

Fuck.

**Notes for the Chapter:**

> Hmm... The constant use of the word daddy is getting on my nerves so I might have to fix it. I thought it'd be sexy for Dean to be out of his mind horny for someone while not knowing their real name, but "Daddy" in every other sentence is getting to be A Lot™. 
> 
> Come join me! mom-i-watch-gay-porn.tumblr.com ! 
> 
> Comments and kudos fuel the fire in my cold dead heart 🥺


	4. Breathless

**Summary for the Chapter:**

> Dean and his boss have some fun and then some more fun after that.

**Notes for the Chapter:**

> Me: says I'll publish this within a week of chapter three  
> also me: takes two months to write the last scene

Dean sulkily picked at his breakfast, the home fries going cold as he dawdled. His ego was bruised and his ass still hurt, despite the soft silk of the panties he’d chosen that morning, a plain black colour, fabric smooth against his skin. 

“You don’t have to eat it,” the Boss said, “You can order something else if you don’t like what they’ve made.” 

“It’s fine, I’m just not very hungry,” Dean replied, setting his fork down, “Daddy,” he added hastily. 

Without another word, the Boss stood up, motioning for Dean to follow him. Back to the office, Dean supposed, hoping for another nap on the couch. 

Instead, his Boss tugged him around the desk, pulling out his big leather office chair. 

“Get under the desk,” he said, as though that was an entirely normal thing to do. 

There was an odd stand under there, with padded sections. Dean sank to his knees but hesitated, unsure of how to proceed. 

“You sit in it, and lean forward,” the Boss said, sitting down to watch as Dean figured out what to do. 

There was a cushioned area to rest his chest against, and padding for his knees. It made sense then, he realized, his head was bound to be right in the Boss’s lap once he was sitting at the desk properly. 

“Good boy,” his Boss said as he climbed into position, “A few rules. Don’t make any noise, I need peace and quiet. Try not to move. I don’t need you to blow me, I’ll let you know when it’s time for that. If you need the bathroom or something, you can tap my leg three times and I’ll let you up if we’re alone." 

Alone. 

If they were alone. 

“Is that clear?” his Boss was saying as Dean tried to fumble his way into comprehending the full scope of what he’d just heard. 

“Uh, yes,” Dean said, entering a bit of a blind panic, “Don’t move, don’t talk, don’t suck your dick. Aye aye, Captain.” 

“Put these on,” his Boss said, handing him a pair of noise cancelling earmuffs and a sleeping mask that was a soft baby pink. It said ‘Princess’ on the front in gold cursive lettering. 

For fuck’s sake. 

Dean’s face flushed as he slid the eye mask on, securing the elastic behind his head. Once he added the ear muffs, he couldn’t see a damn thing, and the only sound was a gentle ringing in his ears, probably from a decade or two of turning his music up too loud. 

He felt fingers stroke against his warm cheeks, and then knees on either side of his torso. His arms were just kind of hanging there, and he wasn’t sure what to do with them, deciding to place them on his Boss’ calf muscles, which were firm and solid under the expensive wool of his suit. 

He rested there for a moment, waiting for the inevitable, already unsure of how long he’d been without his senses. Surely not more than a minute, at most. 

He felt fabric shifting against his chin, his Boss scooting forward a little, and then there was skin pressed against his lips, soft and silky, the unmistakable blunt head of a cock. He opened his mouth, letting it slide between his lips, resting heavy on his tongue. It felt big. 

Fuck, it felt huge. If he wasn’t careful his jaw was going to ache. There were a few more moments of shuffling, adjusting their positions until his mouth was full, cock head pressing almost uncomfortably at his throat, and then they settled. 

His mouth started watering almost immediately, saliva pooling in his mouth as he tried not to dribble onto his Boss’ pants. He also didn’t want to swish it around too much, knowing it would be too stimulating. 

After a couple of minutes, he had no choice but to swallow it, feeling himself make a disgusting slurping noise as he made sure to get it all. He was thanked with a sharp pinch to the neck, fingers gripping tight at his skin. He let out an undignified squeak, and suddenly he felt fingers gripping tight in his hair, yanking him away from the cock before a slap was delivered to his cheek. A solid one too, his Boss didn’t seem to bother warming him up with any love taps. 

His head was forced down again, while the Boss shoved his cock roughly into Dean’s mouth. It was definitely at half-mast now, Dean noticed, adjusting as much as he could without moving. 

His face stung, and Dean felt like sulking. He was just trying to avoid getting spit everywhere, but if the Boss wanted a drooling mess in his pants, then a drooling mess he would get. 

Dean let it all go, not caring when he felt spit sliding past his lips to slide, wet and nasty, down his Boss’ shaft. He rolled his eyes behind the god-awful mask when he was rewarded with a gentle head rub for his efforts, fingers combing through his hair for a moment before leaving again. 

Dean stayed like that for longer than he could guess, thumbs rubbing idle circles on his Boss’ thick calves. Then a deep noise cut through the silence, like a door closing. He felt the vibrations of foot steps across the floor. And then more movement, he wasn’t sure what. 

He tensed up, fingers tightening as he wondered how many people were in the room while he warmed his Boss’ cock in his mouth, wearing a pink princess eye-mask and silk panties. If anyone came around behind the desk, they’d be able to see him no problem, chin shiny with drool and a thick hefty dick between his lips. His cheeks burned at the thought of it, of anyone seeing him like this, nothing but a warm wet hole for a man with too much power. 

He hoped that his boss wasn’t into being watched. Or, he thought as his blood ran cold, his Boss might want to share him. Dean was a private person, he couldn’t imagine how he might feel if he was forced to suck dick in a room full of people. Or suck the dicks of a room full of people. 

His grip tightened, vice-like, around his Boss’ ankles. He felt a hand on his shoulder, the warmth of his Boss’ palm pressed into his skin. Meant to soothe him, to help him settle. 

It kept him from going into an all-out panic, the calming weight of it against his skin. He focused on the feel of it as he heard the faint sounds of voices, people talking. His Boss was having a meeting it seemed. 

Dean focused on keeping a quiet as he could, holding still and doing the job he’d been given. Eventually he felt the tension leave his shoulders, blind-panic clearing as he tuned out the muffled drone of the meeting going on above him. 

It seemed like they really didn’t know; that Dean was tucked just out of sight, his Boss’ secret toy. The thought had him hot and bothered, his dick hardening, filling out his pretty silk panties, straining against the soft fabric. Suddenly he wanted nothing more than to suck the cock in his mouth, but he wasn’t allowed. He struggled not to move his hips, to rub himself against the padded fabric in front of him. In an instant, this whole exercise had turned from one of patience into one of restraint. 

Finally, after what felt like eons, he felt the shuffle of feet again, muffled noises fading away as people left the room. Finally, the door swung shut. 

The earmuffs were people pulled from his head, although the mask stayed firmly in place. 

“You did very well,” his Boss said, “You made a boring meeting much more bearable.” 

Dean moaned, unable to say anything, hands moving to clutch at his Boss’ thighs as if to beg for what he wanted. 

“I think I’d like to use you now,” his Boss said, and a thrill ran through Dean right to the pit of his stomach. 

Fingers tightened in his hair again, and his Boss started moving his head for him, pushing Dean down onto his cock before dragging him off again, his hips shoving upwards on the downstroke. It felt incredible, and Dean put himself to work, trying to do all the things he remembered liking about blow jobs. 

He used his tongue a little, but his Boss seemed mostly content to just fuck his face, so Dean focused on sucking at the right times and keeping himself from gagging when he got too much cock too close to the back of his throat. Dean was hard, loving the feeling of being used, his cock making a damp patch on the front of his pretty underwear. 

“Fuck, you feel so good,” his Boss said, sinking in deep, pushing Dean as far down on his cock as he would go. 

Then Dean felt fingers on his nose, pinching him, and suddenly he couldn’t breathe. He couldn’t pull his head back, and when he tried to open his mouth wider, his Boss would just push in more, filling him up, cock nudging at his throat. 

Dean moaned again, desperate this time. He couldn’t see anything, eyes hidden behind the mask, and fuck if this wasn’t terrifying. His eyes started watering, his vision going fuzzy even though all he could see was darkness. His hands scrabbled at the Boss’ thighs, trying to push himself away. He wouldn’t budge. 

He started feeling faint, his hands clumsy from the lack of oxygen, when he felt a sharp tug on his hair, the cock slipping from his mouth to let sweet, cold air rush into his lungs. He gasped it in, coughing a little, as relief flooded through him. 

“Daddy..,” he croaked, his voice sounding as raw as he felt. 

All he got for his troubles was his Boss’ thick cock back in his mouth, thrusting into him hard as he tried to keep up. It was only a few minutes until he could hear ragged breathing above him, the rhythm growing erratic as his Boss slowed to a stop, fucking in deep one last time and coming, splattering against the roof of Dean’s mouth. 

It didn’t taste amazing, but Dean knew better than to try and spit it out, swallowing down everything his Boss had spent. 

“I’m going to go wash off. Stay put,” his Boss said, sounding a little breathless as he stood and left the room. 

Dean was left, half hard and fully dazed, resting on his little stand under the desk. He felt embarrassed for panicking, knowing that his Boss wouldn’t let him die, not when he’d only managed to work off about sixty dollars of his dipshit father’s debt. 

Although, the guy did seem a little unhinged. Maybe he wouldn’t care if Dean died, knowing John had another son if he got bored of the first. The thought made Dean sick. He’d need to figure out a way to make himself indispensable. 

It might not even be that difficult. So far the sex had been stupidly hot, even the asphyxiation got him going a little. Until it didn’t. 

“Alright,” he heard the Boss say, walking back into the room, “You can get up now, I don’t want you getting all cramped up.” 

Dean was still blindfolded, but he managed to un-straddle the stand, and crawl out from under the desk. He was kneeling on the soft carpet when suddenly he could see again, the sleep-mask pulled from his head and discarded on the desk behind him. He stood up, blinking a bit in the bright light of the midday sun coming in the huge windows. 

“Well, look at you,” his Boss said, stepping closer and fondling the obvious bulge in Dean’s lounge-pants, “Been enjoying yourself?” 

“Yes, Daddy,” Dean said, his cheeks flushing again. 

“Which part did you like?” his Boss asked, “Tell me.” 

“I liked..,” Dean struggled to say it, “I liked you in my mouth.” 

“Is that all?” 

“I don’t know,” Dean said, ducking his head. 

“Come here,” his Boss said, sitting in his big chair and pulling Dean down with him, until he was sitting neatly in his lap. He held Dean close, leaving a soft kiss or two on the side of his neck. 

“Tell me what you liked,” Daddy murmured, his voice low and a little threatening against Dean’s ear. One of his hands lay gently in Dean’s lap, right over his erection. 

“I—All of it,” Dean choked out, fists clenched as he blushed hard. 

“When you kept me warm?” 

“Yes.” 

“And, what else?” 

“I liked,” Dean steeled himself to say it, “I liked being down there, being used.”

Fuck, he was getting properly hard now, his dick straining against the silk in his pants. 

“And the meeting?” 

“Yeah,” Dean said, closing his eyes in embarrassment, his face hot with shame.

“Tell me,” Daddy said, his voice demanding, squeezing Dean’s dick a little, almost like a threat. 

“No one knew I was there,” Dean whispered, arching into the touch, “I thought you might let people watch, or touch me, but you didn’t. I was hidden away, just for you. It was hot.” 

“You liked being my dirty little secret?” 

“Yes, Daddy,” Dean said, dizzy with the need to get that strong hand in his pants.

“Good boy,” Daddy murmured, and it earned him another kiss, wet and hot against his jawline, “And after, when I held your nose? Did you like that?” 

Dean took a sharp breath in, turning his head as if to hide it in Daddy’s shoulder, but Daddy wouldn’t let him. Why he was even admitting to any of this was beyond him. Daddy just seemed to get every little thought out of his head. 

“That was good at first,” he said, his voice barely above a whisper, “But it was... I thought you might kill me.” 

“I could kill you,” Daddy said, just as quiet, “But I’m not going to. Remember that.” 

Dean nodded, hoping he could take Daddy at his word. 

“Do you want to come?” Daddy asked him, gently rubbing at Dean’s bulge. 

“Yes please,” Dean said. 

“Okay,” Daddy said, “Stand up.” 

Dean clambered off of Daddy’s lap, missing the warmth he felt from being held by strong arms. He felt one hand yank at his lounge pants, and then fell easily to the floor, leaving him in his silk panties, stretched tight around his cock. 

“These are very pretty,” Daddy said, running his thumb down the line of Dean’s sick, the nail digging in through the fabric, “Leave them on. Sit on the desk.” 

Dean did as he was told, sitting on the desk in front of Daddy, not making a sound as his legs were pushed wide open, leaving him entirely on display. Daddy leaned back, gesturing with one hand, giving Dean the go-ahead. 

Dean palmed himself over the silk, wanting to take the opportunity to show off. He ran his other hand over his chest, his touch light until he got to a nipple, where he began pinching and rolling it through the fabric of his shirt. Daddy watched him with an impassive face, but his eyes followed every movement he made. He ran a finger along his length, a delicate touch that seemed at odds with how hard Dean was, how turned on he felt in that moment. 

He closed his eyes, rubbing at the damp spot a little before bringing his finger back up to his mouth to suck on, like his own pre-come was the best tasting thing in the world. He let out a little moan, noises he hoped Daddy liked, letting his head tip back as though lost in ecstasy. He felt eyes on him as he moved, but he took his time, wanting to drag this moment out.

Finally, Dean reached inside his panties, fondling his dick, stroking it slowly with a loose fist, trying to keep it out of sight. 

Daddy looked up at him, raising an eyebrow, but Dean just smiled innocently, knowing what his Daddy wanted but not giving it to him. He relented before long, the need for more overwhelming the desire to tease. He tucked the band of his panties behind his sac and got to work, stroking his cock in one hand while rolling his balls with the other. 

He wanted to fuck into his fist, but balance was hard when he was perched like this on the edge of the desk, with his knees pressed as far as they could go to either side. Instead he settled for watching Daddy watch him, twisting his hand on the upstroke, slow and firm, his eyes hooded as he put on a show. He was close, breathing hard as he worked his hand over himself. 

“Stop,” came Daddy’s voice from the chair, and Dean’s hand slowed, falling against his thigh. 

Daddy stared at him a little, watching him as Dean caught his breath, trying not to touch himself. 

“Are you being a tease?” his Daddy asked, pinning him with a firm look, his eyes piercing right through Dean. 

“A little,” Dean admitted, “Just for fun.” 

“More than a little,” Daddy said. 

“It’s sexy,” Dean said, “It adds anticipation.” 

“I don’t like being teased,” Daddy said, “I like getting what I want when I ask for it.” 

“Yes, Daddy,” Dean murmured, aware that this man had probably never been told no in his life. 

“Get on with it,” Daddy said, eyes flicking down to where Dean’s cock still stood, hard and leaking, “And take your shirt off.” 

Dean had his t-shirt off in seconds, tossing it somewhere on the floor before taking himself in hand again. It was less than a minute before Dean was back on the cusp, his thighs straining as he tried to shove into the tight circle of his fist, so close to the edge, almost out of his mind. 

“Stop.” 

Dean whined, balling his hands up against the desk as he struggled not to touch himself. 

“Is this sexy?” Daddy asked, “Do you feel this is increasing your enjoyment, by adding anticipation?” 

“I mean..,” Dean was panting, “It’s frustrating, but yeah. It’s pretty sexy.” 

Daddy regarded him for a second, before scooting a little closer. He stretched a hand out and took Dean by the balls, cradling them gently. 

“Carry on,” he said. 

Dean stroked himself in earnest, feeling like he was about to burst out of his skin, wanting to come so badly, but also wanting to see where this was going. Just as he settled back into the rhythm of things, Daddy squeezed his balls, his grip vice-like, until Dean let out a sharp gasp. 

“I didn’t tell you to stop,” Daddy said, and Dean did as he was told, jerking off as quickly as possible, desperate to finish before things escalated. 

The pressure on his balls lessened, and Daddy was back to fondling them. Dean had never really been one to get his balls hurt but he had to admit, this was really doing it for him. Maybe it was the edging, or the powerful man in front of him, but within a few strokes, Dean was already close again, right on the brink of coming. 

He had his head tipped back in pleasure, eyes falling shut as he jacked his dick, and then Daddy squeezed him again, hard, and that was all it took before Dean came, spurting his release all over his own chest. He stroked himself through it, tipping his head down to look at Daddy, just in time to see him move forward and lick a stripe right through Dean’s come. 

He made sure to cover every part of Dean’s chest, collecting every stray drop on his tongue, before he moved up to kiss Dean, their lips brushing slightly before Daddy pushed a sloppy load of Dean’s come into his own mouth. They made out, pressed against the desk and snowballing his spend back and forward between them in the filthiest kiss Dean had had in a long, long time. If he hadn’t just jizzed all over himself, this alone would have got him harder than diamonds. 

“Mm,” Daddy said, pulling away from him, “Maybe a little anticipation can be a good thing.” 

Dean laughed, hopping down from the desk and tucking away his dick. His legs felt like jelly, his whole body loose and relaxed. 

Daddy pulled him close, kissing him again, nipping at his bottom lip. 

“Go to the living room, we’ll have some lunch,” he said, running his lips along Dean’s neck. 

Dean left the room in nothing but his silk panties, and waited for Daddy stretched out on the ottoman, lounging in what he hoped was an alluring fashion. 

When Dean got home that evening, there were another three hundred dollars in his pants, tucked down the back this time, bills slightly crumpled from having sat on them for an hour. 

He sighed, turning them over in his hands. Two days work, getting freaky with a stupidly handsome man, and he’d already made enough to pay most of his rent for the month. For the first time in a long time, he had cash to burn. He felt a strong urge to spend it all on something stupid, like a new leather jacket, or a play station. Instead he tucked it away in a beat-up old coffee can that lived under his bed, with the other three hundred dollars and some other wrinkled bills that he’d kept for emergencies. 

It was officially the weekend. He had two whole days to himself to unwind, to spend alone in an empty, cold apartment, missing his brother and trying to process what the fuck was happening with his “job”. He took one of the old twenties from the coffee can, with a plan to order a pizza and fall asleep on the couch. 

He spent his days off alone. He had stale cereal for breakfast, having accidentally left the box open the last time he used it, over a week ago. It paled in comparison to how he ate at work, so he tried to distract himself, googling how to get semen out of silk and lace. Then he succumbed to the restless urge he had to deep clean the apartment, scraping grout and scrubbing tiles until his arms felt numb. Sunday was much the same, except in between vacuuming and cleaning the fridge, he got to talk to Sam. It wasn’t a lot, but he felt more human for it. 

Dean expected it to be a boring couple of days. What he didn’t expect was the knock on his door at nearly eight o’clock. Looking through the peephole, he saw it was one of the goons. He undid the locks, standing there in his threadbare pajamas, annoyed and ready to argue. 

“You’re early,” he said as he swung the door open. 

“Put your shoes on, you’re comin’ in,” the goon said. 

“What?” Dean said, pulling his phone out of his pocket to check the time. 

“Hurry up, I’m supposed to deliver you ‘A-S-A-P’ or whatever,” the goon said, rolling his eyes. 

“Fine. Let me just get dressed,” Dean said, moving to shut the door again, only to find his way blocked by a big thick arm against the wood. 

“No,” the goon said, “Get your shoes on, we’re going now. Boss’s orders.” 

Dean hesitated, wanting to change out of his pajamas, but knowing very well what would happen if ‘Boss’s orders’ weren’t followed. 

“Fine,” he said finally, stuffing his feet into his boots before grabbing his wallet and a jacket. 

It was freezing outside, and Dean huffed as he followed today’s goon to the big black SUV parked in the street. He hoped this one had seat warmers. 

He spent most of the drive lost in thought, staring out the window as he wondered what the boss could want with him. It probably wasn’t anything bad, he figured, and as much as he wanted to be annoyed by the idea of driving an hour to give a blowjob, he found he couldn’t be. If anything, the idea excited him, that he could just be summoned from wherever on a whim, because his boss wanted to use his body for pleasure. 

He wished he’d changed into his jeans after all, as he felt himself harden a little, the bulge obvious through the thin flannelette of his pajama pants. It was only because he was trying to distract himself that he noticed they hadn’t left the freeway, seemingly driving past Chicago instead of heading downtown. 

“Hey, where are you taking me?” he asked, fantasy forgotten as he realized he hadn’t put much effort into double checking the identity of the man who’d come to collect him. 

“To the boss,” the man replied, never taking his eyes off the road. 

“Office is behind us,” Dean said, tension coursing through him. 

“Not goin’ to the office,” the goon said, “Boss is at home.” 

“He doesn’t live in the city?” Dean asked. 

“None of your business,” was the reply, “Speaking of, put this on.” 

A thick black bag was tossed into the backseat, meant to go over Dean’s head, he assumed. 

“No way,” Dean said, “You could be anybody.” 

The goon laughed.

“Listen kid, if you think you get to see where the Boss lives and come out of it alive, that’s your business. He’ll be real sorry to see your fruity ass go, I bet.” 

“You get to see where he lives,” Dean pointed out, black bag clenched in one fist. 

“I’ve been with the organization for fifteen years. You haven’t. Put the bag on,” the goon replied. 

Dean thought about that for a moment, realizing it was probably his best bet to just go along with it. The chances of him being kidnapped were slim, and it probably was best to do everything he could to ensure his Boss’s privacy remained intact, lest he face the consequences. He slipped the bag over his head, and tried not to freak out about it. 

He wasn’t sure how long it was before the car slowed and finally came to a stop. His footsteps echoed, so he must have been in some kind of garage. The goon wasn’t very helpful as he led Dean through a series of hallways and stumbling up a set of stairs before shoving him into a room. 

“Wait here,” he said, “Leave the bag on.” 

The door clicked shut behind him, and then Dean was alone. 

“Hello?” he called out, just to be sure. 

When he got no answer, he put his hands out in front of him and began walking slowly. Just as he started to wonder how big this room was, he bumped into something soft, knees pressing into what had to be a mattress. He turned and sat down to wait, figuring that he hadn’t been told not to, so why not take the liberty. 

He wasn’t sure how long he waited, but it felt like an age. Anticipation built in his gut, hoping that he was here to put the mattress beneath him to good use. Maybe the boss would finally fuck him. Dean’s stomach did a pleasant flip at the thought of it. 

Eventually he heard the door open and close again; felt a presence in the room with him. He sat up straighter, hoping it was his boss coming to put him to good use. 

He heard the muffled sound of footsteps on soft carpet, and then curtains being pulled behind him, and then finally, finally, felt a warm hand against his shoulder that he instantly knew belonged to his boss. 

The bag was pulled up and off his head, revealing his boss standing in front of him, bathed softly in lamp-light and looking comfortable in casual clothes in the middle of a spacious modern looking bedroom. 

“Hello,” Boss said, his deep voice flowing over Dean like hot water in a shower. 

“Hi Daddy,” Dean said, sounding a lot more breathless than he’d ever admit to. 

“Thank you for coming on short notice,” Boss said, fingers tracing the line of Dean’s neck, “I’ve had a long, frustrating day, and I wanted you.” 

Dean nodded, fully committed to the task of making his boss feel better. He watched as his boss moved away from him, beginning to get undressed. First his shirt, then his pants, off and into a hamper by the door to what Dean assumed was an ensuite. He itched with the need to get his hands on the miles of tan skin that was newly exposed. His boss was kinda stacked, Dean realized; sturdy shoulders and thick thighs, broad chested with muscular arms. He couldn’t look away. 

“Come here,” Boss said as he climbed into bed, indicating for Dean to do the same. 

Dean followed, lifting up the soft covers and sliding beneath them, scooting closer to the middle of the bed as his boss pulled him in. A strong hand slid up under his t-shirt, and Dean helped to tug it off over his head, tossed somewhere behind him. 

Then they were chest to chest, and Dean had his hands full of warm skin and muscle, taking every opportunity to feel his boss up, rubbing at a nipple, squeezing whenever he felt a particularly good spot. Boss was doing the same, strong hands against his back, one pushing into his pajamas and groping at his cheeks. Their noses brushed, just breathing in each other’s space until his boss pushed forward and pressed their lips together. 

Dean felt a thrill go through him, the feeling of being held and kissed like he was something to be treasured overwhelming him a little, and then he was clinging onto his boss for dear life. 

“I want these raggedy pants off,” his Boss said, and Dean was quick to oblige him, shucking his pajama pants over his hips and down his legs, losing them somewhere in the blankets. 

He felt his boss do the same, and then suddenly they were pressed together, nothing but skin on skin, entirely bare. His boss hauled him in ever closer somehow, pulling Dean’s knee up over his hip, one of those incredible thighs nudging between his legs. 

Dean was already most of the way hard, and his boss wasn’t far behind him, their cocks tucked snug between them. 

“Oh, fuck,” Dean moaned, as his boss started rolling their hips together, creating a slow but steady rhythm. 

“Do you like this?” his boss murmured, low and gravelly right next to Dean’s ear. 

“Yeah,” Dean replied, hoping he didn’t sound as breathless as he felt, “Feels so good, Daddy.” 

“Good,” Daddy said, nipping at Dean’s lips one more time before rolling them over, Dean on his back with his legs hitched up around his Daddy’s waist, the heavy weight of him delicious. 

They tried to keep kissing, but soon the movement was too much and all they could do was pant against each other’s mouths as Daddy rocked their hips together. Dean was moaning, already half out of his mind with pleasure, daddy’s cock hard and leaking against his own, sliding sweetly together in the tight space between them. He clung to Daddy, meeting every thrust as best he could, looking up at him through half lidded eyes, fighting hard to stay present and not lose himself in feeling. 

Daddy let out a groan then, burying his face against Dean’s neck. He reached between them and wrapped one of his strong hands around both of their cocks, fucking into the tunnel of his fist, his thrusts jostling Dean until Dean was shoving into his hand too. It wasn’t long before their rhythm faltered, faster and sloppier as they got closer to the edge. Daddy’s hand was squeezing them a little, his fingers rubbing over their sensitive heads and Dean felt himself pull tight and then snap, moaning loud and open mouthed as his come spurted out against his skin, dribbling over Daddy’s fist. 

Daddy wasn’t far behind him, grunting as he bit down on the skin of Dean’s neck, his hips stuttering and coming to a stop as he milked himself. Dean held him close as he breathed through it. Daddy pressed a few soft kisses to the bite mark he’d left behind, before rolling off of Dean, who was sorry to see him go. 

Dean drifted for a moment, sated and warm in the most comfortable bed he’d ever experienced, and jumped a little when he felt a warm washcloth against his stomach. 

“Let me just clean you up, then you can rest,” Daddy murmured to him, his touch gentle and caring. It did weird things to Dean’s gut. 

Before he could think too much about it, the lights were switched off and Daddy was back in bed with him, pulling Dean close until they were spooned together, Daddy’s warm breath against his nape and one arm slung around his waist. 

“I’m gonna wake you up with a blow job,” Dean murmured into the dark. 

He felt the laugh rumble through Daddy’s chest, and a kiss against his shoulder, and then he was drifting off to sleep. 

It was the best sleep Dean had had in years, long and unbroken. When he woke, face down in the pillows, it was still before dawn, but that didn’t mean much in winter. He rolled over, looking for his bed mate, finding him on his back and snoring gently. It was cute. 

Dean stretched a little and then got to work, slipping below the blankets to find where Daddy’s cock lay soft against his hip. It was dark beneath the sheets, so Dean worked by feel, pressing sloppy open mouthed kisses along Daddy’s shaft, licking at him gently, slowly getting him hard. Just as he started laving his tongue over and around the tip of Daddy’s cock, there was a noise in the hallway and suddenly the bedroom door was slamming open. 

“Wake up, Cassie! There’s fun to be had,” came a man’s voice, shattering the early morning quiet. 

Dean froze, cock head slipping from his mouth. 

“Come on, time to get up Castiel,” came the voice again, and Dean felt his boss—Castiel, grumble and shift, rolling away from him. 

There was the sound of curtains being opened. A warm knee bumped into his chest. And then, quite suddenly, there was a hand at the back of Dean’s neck, gripping him so tightly he winced. 

“Gabriel,” came his Boss’s voice, “Get out.” 

“Fine,” Gabriel replied, “You’re no fun. We’re all downstairs, come for cocoa when you’re done being grumpy.” 

There were footsteps and then the door shut again. Suddenly Dean was pulled bodily up the bed, out from under the covers, the fingers digging into his neck so hard that they were likely to leave a mark. 

His boss stared at him, hard, his eyes glinting dangerously in the low light of the bedside lamp. It was a dramatic shift from the soft gaze of the night before. 

“What did you hear,” he asked, voice low. 

“I—,” Dean floundered, not wanting to lie, but also not wanting to get into trouble.

“Answer me,” Castiel demanded, pushing Dean onto his back and holding him there by his neck, the same hand that had jerked him off now threatening to crush his windpipe. 

“I heard, uh,” Dean swallowed hard, “Maybe a nickname, I don’t know. You called him Gabriel,” he finished weakly. 

This man—his boss, Castiel, stared at him in silence. Dean could practically hear the cogs turning in his head. Dean felt himself yanked up off the bed, held by the throat at his boss’ eye level. 

“Breathe a word of this to anyone, and I’ll dismember your brother in front of you, do you understand?” 

Dean nodded frantically, eyes wide with fear. 

“Yes, Daddy,” he croaked out. 

Castiel let go of him then, his torso dropping back onto the bed with a bounce. 

“Get dressed,” he said, “I’ll see you at the office.” 

Dean watched as his boss got up, pulling a thick robe from the closet and shrugging into it. He picked up the black bag from the foot of the bed and tossed it in Dean’s direction without a glance, before leaving the room and shutting the door loudly behind him. 

Dean sat there in his Boss’s bed, naked and rubbing at his sore neck as he tried to take stock of what had just happened. Of all the names he imagined his boss having, Castiel wasn’t one of them. 

He sighed, and moved to get dressed, hoping that he’d somehow forget what he heard. 

He doubted it.

**Notes for the Chapter:**

> hehhhehehhe i figured out the 'Daddy' problem! 
> 
> pls leave a comment if you liked it. Thanks for reading!


End file.
